Regular and red-shifted fluorescence of the donor-acceptor compound 5-(1H-pyrrole-1-yl)thiophenecarbonitrile (TCN) is efficiently quenched by internal modes of thiophene

Physical Chemistry Chemical Physics : PCCP
Mercedes V BohnwagnerAndreas Dreuw

Abstract

The photochemical properties of thiophene analogs of N-pyrrolobenzonitrile (PBN), notably the two isomers 5-(1H-pyrrole-1-yl)thiophene-2-carbonitrile (2-TCN) and 5-(1H-pyrrole-1-yl)thiophene-3-carbonitrile (3-TCN) have been investigated. The aim of this study is to reveal whether the donor-acceptor compound TCN shows a fluorescence behavior similar to other benzonitrile derivatives like PBN and N,N-dimethylaminobenzonitrile (DMABN). For this purpose high-level ab initio methods have been employed comprising approximate coupled cluster (CC2) methods, the algebraic-diagramatic construction scheme for the polarization propagator (ADC(2) and ADC(3)) as well as time-dependent density functional theory (TDDFT). Solvent effects have been included using continuum solvation models. In the gas phase excited TCN molecules most likely deactivate in a radiationless fashion to the ground state via a low lying S1/S0 conical intersection. In polar solvents the dark S(CT) (S2) state is stabilized below S(ππ*) (S1), however, despite this stabilization radiationless decay to the ground state remains the most likely deactivation pathway. Nevertheless, population of a twisted minimum of the S(CT) state becomes energetically feasible. Hence it is pr...Continue Reading

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